JP2005522489A - システインプロテアーゼの可逆性インヒビターとして有用なシアナミド - Google Patents
システインプロテアーゼの可逆性インヒビターとして有用なシアナミド Download PDFInfo
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- JP2005522489A JP2005522489A JP2003583350A JP2003583350A JP2005522489A JP 2005522489 A JP2005522489 A JP 2005522489A JP 2003583350 A JP2003583350 A JP 2003583350A JP 2003583350 A JP2003583350 A JP 2003583350A JP 2005522489 A JP2005522489 A JP 2005522489A
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- Prior art keywords
- alkyl
- compound
- aryl
- morpholinyl
- group
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- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 title claims description 11
- 102000005927 Cysteine Proteases Human genes 0.000 title abstract description 32
- 108010005843 Cysteine Proteases Proteins 0.000 title abstract description 32
- 239000013037 reversible inhibitor Substances 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 207
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 95
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 59
- 201000010099 disease Diseases 0.000 claims abstract description 52
- 238000000034 method Methods 0.000 claims abstract description 47
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 241
- -1 thiopyranyl Chemical group 0.000 claims description 220
- 125000003118 aryl group Chemical group 0.000 claims description 138
- 125000002757 morpholinyl group Chemical group 0.000 claims description 104
- 125000003386 piperidinyl group Chemical group 0.000 claims description 99
- 125000004193 piperazinyl group Chemical group 0.000 claims description 90
- 125000004076 pyridyl group Chemical group 0.000 claims description 90
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims description 86
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 84
- 125000001041 indolyl group Chemical group 0.000 claims description 78
- 125000003545 alkoxy group Chemical group 0.000 claims description 69
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 68
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 65
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 65
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 65
- 125000003387 indolinyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 64
- 125000002541 furyl group Chemical group 0.000 claims description 63
- 125000001544 thienyl group Chemical group 0.000 claims description 61
- 125000004043 oxo group Chemical group O=* 0.000 claims description 60
- 229910052757 nitrogen Inorganic materials 0.000 claims description 59
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims description 59
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 58
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 58
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 57
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 55
- 125000000335 thiazolyl group Chemical group 0.000 claims description 55
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 54
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000002971 oxazolyl group Chemical group 0.000 claims description 52
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 51
- 125000002883 imidazolyl group Chemical group 0.000 claims description 51
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 51
- 125000001624 naphthyl group Chemical group 0.000 claims description 51
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 46
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 claims description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 229940002612 prodrug Drugs 0.000 claims description 45
- 239000000651 prodrug Substances 0.000 claims description 45
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 claims description 45
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 44
- 229910052736 halogen Inorganic materials 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 44
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 44
- 108090000625 Cathepsin K Proteins 0.000 claims description 42
- 102000004171 Cathepsin K Human genes 0.000 claims description 41
- 125000005956 isoquinolyl group Chemical group 0.000 claims description 41
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 41
- 150000003457 sulfones Chemical class 0.000 claims description 41
- 150000003462 sulfoxides Chemical class 0.000 claims description 41
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims description 41
- 229910052760 oxygen Inorganic materials 0.000 claims description 40
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 40
- 239000012453 solvate Substances 0.000 claims description 40
- 125000004434 sulfur atom Chemical group 0.000 claims description 40
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 39
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 39
- 125000005493 quinolyl group Chemical group 0.000 claims description 39
- 150000002367 halogens Chemical class 0.000 claims description 38
- 229910052799 carbon Inorganic materials 0.000 claims description 37
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 36
- 125000004104 aryloxy group Chemical group 0.000 claims description 33
- 125000001589 carboacyl group Chemical group 0.000 claims description 33
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 31
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 30
- 125000004594 isoindolinyl group Chemical group C1(NCC2=CC=CC=C12)* 0.000 claims description 29
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 29
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 28
- 108090000613 Cathepsin S Proteins 0.000 claims description 27
- 125000002795 guanidino group Chemical group C(N)(=N)N* 0.000 claims description 25
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 25
- 102100035654 Cathepsin S Human genes 0.000 claims description 24
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 125000004417 unsaturated alkyl group Chemical group 0.000 claims description 21
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 125000004414 alkyl thio group Chemical group 0.000 claims description 20
- 125000003435 aroyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 230000001404 mediated effect Effects 0.000 claims description 19
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 18
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 18
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 18
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 17
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 16
- 238000011282 treatment Methods 0.000 claims description 16
- 125000004423 acyloxy group Chemical group 0.000 claims description 15
- 125000003282 alkyl amino group Chemical group 0.000 claims description 15
- 125000005333 aroyloxy group Chemical group 0.000 claims description 15
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 12
- 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- 125000000723 dihydrobenzofuranyl group Chemical group O1C(CC2=C1C=CC=C2)* 0.000 claims description 12
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 12
- 125000002393 azetidinyl group Chemical group 0.000 claims description 11
- 125000004603 benzisoxazolyl group Chemical group O1N=C(C2=C1C=CC=C2)* 0.000 claims description 11
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 11
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 11
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 11
- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 claims description 11
- 125000001425 triazolyl group Chemical group 0.000 claims description 11
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims description 10
- 125000004582 dihydrobenzothienyl group Chemical group S1C(CC2=C1C=CC=C2)* 0.000 claims description 10
- 125000005438 isoindazolyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 9
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 claims description 9
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 9
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 claims description 9
- 125000005239 aroylamino group Chemical group 0.000 claims description 9
- 125000005141 aryl amino sulfonyl group Chemical group 0.000 claims description 9
- 125000005162 aryl oxy carbonyl amino group Chemical group 0.000 claims description 9
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 claims description 9
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 9
- 125000004604 benzisothiazolyl group Chemical group S1N=C(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 9
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 9
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 125000005110 aryl thio group Chemical group 0.000 claims description 8
- BVCRERJDOOBZOH-UHFFFAOYSA-N bicyclo[2.2.1]heptanyl Chemical group C1C[C+]2CC[C-]1C2 BVCRERJDOOBZOH-UHFFFAOYSA-N 0.000 claims description 8
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 8
- 125000000623 heterocyclic group Chemical group 0.000 claims description 8
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
- 229940079593 drug Drugs 0.000 claims description 5
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 5
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
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- JWJRTTQZJDDBBU-UHFFFAOYSA-N cyano(nitrocarbonyl)carbamic acid Chemical compound OC(=O)N(C#N)C(=O)[N+]([O-])=O JWJRTTQZJDDBBU-UHFFFAOYSA-N 0.000 claims description 3
- 238000006268 reductive amination reaction Methods 0.000 claims description 3
- DSPHFASHOJAOKN-UHFFFAOYSA-N 1-[(7-oxobenzo[a]phenalen-2-yl)amino]anthracene-9,10-dione Chemical compound C1=CC2=CC(NC3=C4C(=O)C5=CC=CC=C5C(C4=CC=C3)=O)=CC(C=3C(=CC=CC=3)C3=O)=C2C3=C1 DSPHFASHOJAOKN-UHFFFAOYSA-N 0.000 claims description 2
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
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- 238000004519 manufacturing process Methods 0.000 claims 3
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 1
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 32
- 239000003112 inhibitor Substances 0.000 description 28
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 25
- 239000000203 mixture Substances 0.000 description 23
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- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 17
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- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 6
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C261/00—Derivatives of cyanic acid
- C07C261/04—Cyanamides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/06—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Pulmonology (AREA)
- Reproductive Health (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychiatry (AREA)
- Vascular Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Enzymes And Modification Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37036802P | 2002-04-05 | 2002-04-05 | |
| PCT/US2003/009852 WO2003086325A2 (fr) | 2002-04-05 | 2003-04-01 | Cyanamides utiles en tant qu'inhibiteurs reversibles des cysteine proteases |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JP2005522489A true JP2005522489A (ja) | 2005-07-28 |
Family
ID=29250518
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003583350A Pending JP2005522489A (ja) | 2002-04-05 | 2003-04-01 | システインプロテアーゼの可逆性インヒビターとして有用なシアナミド |
Country Status (8)
| Country | Link |
|---|---|
| EP (1) | EP1495009B1 (fr) |
| JP (1) | JP2005522489A (fr) |
| AT (1) | ATE388946T1 (fr) |
| AU (1) | AU2003230772A1 (fr) |
| CA (1) | CA2477692A1 (fr) |
| DE (1) | DE60319686T2 (fr) |
| ES (1) | ES2301793T3 (fr) |
| WO (1) | WO2003086325A2 (fr) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2006076796A1 (fr) * | 2005-01-19 | 2006-07-27 | Merck Frosst Canada Ltd. | Inhibiteurs de la cathepsine k et obesite |
| US8497271B2 (en) | 2009-10-07 | 2013-07-30 | Bristol-Myers Squibb Company | Modulators of G protein-coupled receptor 88 |
| US8304577B2 (en) | 2009-10-09 | 2012-11-06 | Bristol-Myers Squibb Company | Modulators of G protein-coupled receptor 88 |
| US8426414B2 (en) | 2009-10-09 | 2013-04-23 | Bristol-Myers Squibb Company | Modulators of G protein-coupled receptor 88 |
| US8703953B2 (en) | 2012-03-09 | 2014-04-22 | Bristol-Myers Squibb Company | Aryl ether-base kinase inhibitors |
| US8901305B2 (en) | 2012-07-31 | 2014-12-02 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| CN105121445A (zh) | 2013-02-22 | 2015-12-02 | 百时美施贵宝公司 | 作为连接蛋白相关激酶1(AAK1)抑制剂的5H-色烯并[3,4-c]吡啶 |
| US10253027B2 (en) | 2013-07-08 | 2019-04-09 | Bristol-Myers Squibb Company | Aryl lactam kinase inhibitors |
| US10174044B2 (en) | 2015-04-10 | 2019-01-08 | Bristol-Myers Squibb Company | Fused pyridines as kinase inhibitors |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002537293A (ja) * | 1999-02-20 | 2002-11-05 | アストラゼネカ アクチボラグ | カテプシンｌおよび／またはカテプシンｓの阻害剤としてのアセタミドアセトニトリル誘導体 |
| JP2003530384A (ja) * | 2000-04-06 | 2003-10-14 | メルク フロスト カナダ アンド カンパニー | カテプシンシステインプロテアーゼ阻害薬 |
-
2003
- 2003-04-01 ES ES03723865T patent/ES2301793T3/es not_active Expired - Lifetime
- 2003-04-01 CA CA002477692A patent/CA2477692A1/fr not_active Abandoned
- 2003-04-01 EP EP03723865A patent/EP1495009B1/fr not_active Expired - Lifetime
- 2003-04-01 JP JP2003583350A patent/JP2005522489A/ja active Pending
- 2003-04-01 AU AU2003230772A patent/AU2003230772A1/en not_active Abandoned
- 2003-04-01 DE DE60319686T patent/DE60319686T2/de not_active Expired - Fee Related
- 2003-04-01 AT AT03723865T patent/ATE388946T1/de not_active IP Right Cessation
- 2003-04-01 WO PCT/US2003/009852 patent/WO2003086325A2/fr active Search and Examination
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2002537293A (ja) * | 1999-02-20 | 2002-11-05 | アストラゼネカ アクチボラグ | カテプシンｌおよび／またはカテプシンｓの阻害剤としてのアセタミドアセトニトリル誘導体 |
| JP2003530384A (ja) * | 2000-04-06 | 2003-10-14 | メルク フロスト カナダ アンド カンパニー | カテプシンシステインプロテアーゼ阻害薬 |
Non-Patent Citations (1)
| Title |
|---|
| JPN6009046864, Ｃｈｅｍｉｃａｌ Ａｂｓｔｒａｃｔｓ, 1956 * |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2301793T3 (es) | 2008-07-01 |
| EP1495009A2 (fr) | 2005-01-12 |
| DE60319686D1 (de) | 2008-04-24 |
| DE60319686T2 (de) | 2009-04-16 |
| WO2003086325A2 (fr) | 2003-10-23 |
| WO2003086325A3 (fr) | 2004-07-01 |
| AU2003230772A1 (en) | 2003-10-27 |
| ATE388946T1 (de) | 2008-03-15 |
| EP1495009B1 (fr) | 2008-03-12 |
| AU2003230772A8 (en) | 2003-10-27 |
| CA2477692A1 (fr) | 2003-10-23 |
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